EP0041448B1 - Disinfecting composition containing a quaternary ammonium and an oligomer of hexamethylene-diguanide hydrochloride - Google Patents
Disinfecting composition containing a quaternary ammonium and an oligomer of hexamethylene-diguanide hydrochloride Download PDFInfo
- Publication number
- EP0041448B1 EP0041448B1 EP81400848A EP81400848A EP0041448B1 EP 0041448 B1 EP0041448 B1 EP 0041448B1 EP 81400848 A EP81400848 A EP 81400848A EP 81400848 A EP81400848 A EP 81400848A EP 0041448 B1 EP0041448 B1 EP 0041448B1
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- EP
- European Patent Office
- Prior art keywords
- oligomer
- hydrochloride
- hexamethylene
- quaternary ammonium
- diguanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
Definitions
- the present invention relates to a new disinfectant composition which acts very quickly and strongly.
- French Patent 2,390,100 describes compositions containing a quaternary ammonium derivative and a guanid component, specifying that such a combination had been made for the protection of wood and wood-based materials against destructive fungi.
- This product is not very toxic (the lethal dose-DL-50 is more than 5000 mg per kg) and the concentration of use does not cause irritation of the skin or the eyes. It is known to be non-allergenic to the skin and is free from systemic toxicity through the epidermis.
- hexamethylene biguanide hydrochloride seems to be better than that of chlorhexidine salts because of the very great instability of these latter products in the light; in the presence of most surfactants they have a slight variation in pH, in the presence of hypochlorite they are transformed into an indelible red dye and finally there is the possibility of the formation of chloraniline, a product considered to be metabolizing and toxic.
- the hexamethylene biguanide hydrochloride oligomer has none of these drawbacks. Its bactericidal power is very high and rapid. A 20% solution of this product diluted to 0.25% (i.e.
- OCHB hexamethylene biguanide hydrochloride
- compositions containing 0.1 to 4% by weight of an oligomer of hexamethylene biguanide hydrochloride (OCHB) and 0.01 to 1.5% by weight of didecyldimethylammonium chloride (CDDA) exhibit bactericidal and fungicidal activities much higher than those obtained by using equivalent amounts of the products forming said composition.
- OCHB hexamethylene biguanide hydrochloride
- CDDA didecyldimethylammonium chloride
- This mixture is particularly suitable when used with a film-forming polymer, since the deposited film rapidly destroys all microorganisms on the surface and remains germicidal for a very long time.
- didecyl dimethylammonium in the compositions according to the invention has in particular a certain advantage, because of its very high wetting power by lowering the surface tension of the mixture to 2.81 N / m 2 approximately.
- composition according to the invention contains from 0.01% to 1.5% of CDDA and from 0.1 to 4% of OCHB. It is an aqueous and / or alcoholic solution.
- OCHB is used in solution in distilled water. An inoculum of a microorganism is added at a given concentration. After 3 minutes, the surviving bacteria are counted and the result is expressed as a power of 10.
- the drop in microorganisms is therefore 10 4 / ml.
- the bactericidal activity in vivo of such a composition is determined.
- This solution is used as a disinfectant for hospital staff, the hands of surgeons, various surfaces that may be contaminated, X-ray machines, surgical instruments, etc.
- This composition, used at 4% is one of the most powerful sterilants for surgical instruments.
- a solution for washing wounds or the skin is prepared, having the composition below:
- An afterglow lacquer having the following composition is prepared:
- the bactericidal activity is determined according to the Gashen method. A group of three women and three men wash their hands with soap for one minute, then rinse their hands with water and dry them. Finally, after 60 min. waiting, there are flora on each hand. The solution according to the invention is applied for a min. on each right hand, the left hand serving as a reference. The following results are obtained (Table VI):
- the activity of the disinfectant apparently remains as good after wearing the glove for one hour, since the bacterial population remains at the same level as after the action of the product for one minute. The persistence of action is therefore very good for this lacquer.
- lacquer solution pH fixed between 6.5 and 6.8.
- This product is used to water contaminated surfaces (as it is diluted) and it destroys all microorganisms on the surface (gram + and - bacteria, yeasts, spores, viruses) and forms a light film having an afterglow which makes it possible to destroy all fallout from surrounding germs. It is used as is for cold sterilization of the internal circuit of hemodialysis machine (artificial kidney), for cold sterilization of surgical, medical and internal examination instruments and equipment (endoscope ...) . It destroys cold all microorganisms, bacteria ⁇ , viruses, spores, fungi. The presence of polyvinyl pirrolidone polymer keeps soilings in suspension and prevents their redeposition.
Abstract
Description
La présente invention concerne une nouvelle composition désinfectante agissant très rapidement et fortement.The present invention relates to a new disinfectant composition which acts very quickly and strongly.
Le brevet français 2 390 100 décrit des compositions contenant un dérivé d'ammonium quaternaire et un composant guanidé en spécifiant qu'une telle association avait été réalisée pour la protection du bois et des matières à base de bois contre les champignons destructeurs.French Patent 2,390,100 describes compositions containing a quaternary ammonium derivative and a guanid component, specifying that such a combination had been made for the protection of wood and wood-based materials against destructive fungi.
Dans le brevet français 2 342 074 du demandeur, on a décrit des produits désinfectants à rémanence d'action, à savoir ayant une action prolongée dans le temps, et on a fait état dans cette publication d'un procédé de dépôt d'un polymère filmogène contenant au moins un désinfectant qui confère à la pellicule formée une action bactéricide vis-à-vis des germes qui pourraient se déposer sur celle-ci et qui proviendraient de l'air ambiant ou qui seraient déposés par contact. Une des conditions mentionnées dans ce brevet est une parfaite comptabilité entre les germicides, les solvants, les polymères ou copolymères, et les autres additifs possibles. Il est toutefois essentiel que le ou les germicides fassent preuve d'une efficacité maximum en ce qui concerne la vitesse de destruction des microorganismes et que le spectre d'activité soit le plus large possible.In French patent 2 342 074 of the applicant, disinfectant products with long-lasting action, that is to say having a prolonged action over time, have been described, and a method of depositing a polymer has been reported in this publication. film-forming agent containing at least one disinfectant which gives the formed film a bactericidal action against germs which could be deposited thereon and which would come from the ambient air or which would be deposited by contact. One of the conditions mentioned in this patent is perfect compatibility between germicides, solvents, polymers or copolymers, and the other possible additives. However, it is essential that the germicide (s) demonstrate maximum effectiveness with regard to the rate of destruction of microorganisms and that the spectrum of activity is as wide as possible.
Selon la présente invention, on a cherché à élargir le champ d'application du brevet 2 342 074, utilisant des compositions sur des surfaces inertes telles que murs, plafonds, poignées de portes et chariots ou tables d'opération et on a voulu déposer des compositions désinfectantes sur la peau humaine, par exemple, pour désinfecter les mains des chirurgiens avant la mise de gants, les mains des infirmières et autre personnel hospitalier. On désire ainsi empêcher la contamination des malades le personnel par et les contaminations croisées entre les malades. On a voulu effectuer la désinfection pré et post-opératoire de la peau, du champ opératoire, laver les plaies, etc.... Il a donc fallu rechercher des bactéricides très puissants mais non irritants et n'ayant pas tendance à pénétrer et diffuser à travers la peau.According to the present invention, attempts have been made to widen the scope of patent 2 342 074, using compositions on inert surfaces such as walls, ceilings, door handles and operating trolleys or tables and we have sought to deposit disinfectant compositions on human skin, for example, to disinfect the hands of surgeons before putting on gloves, the hands of nurses and other hospital staff. It is thus desired to prevent contamination of the sick by staff and cross-contamination between the sick. We wanted to carry out the pre and post-operative disinfection of the skin, the operating field, wash the wounds, etc. We therefore had to look for very powerful but non-irritating bactericides which do not tend to penetrate and diffuse through the skin.
Un des produits qui possède ces caractéristiques (outre les sels de chlohexidine décrits dans le brevet mentionné ci-dessus) est l'oligomère (n=4 à 7) de chlorhydrate d'hexaméthylène biguanide décrit dans le brevets anglais n° 702 268 et 1 167 249. Ce produit est très peu toxique (la dose léthale-DL-50 est de plus de 5000 mg par kg) et la concentration d'utilisation ne provoque pas d'irritation de la peau ni des yeux. Il est connu comme étant non allergène pour la peau et il est exempt de toxicité systémique à travers l'épiderme.One of the products which has these characteristics (in addition to the chlohexidine salts described in the patent mentioned above) is the oligomer (n = 4 to 7) of hexamethylene biguanide hydrochloride described in English patent Nos. 702 268 and 1 167 249. This product is not very toxic (the lethal dose-DL-50 is more than 5000 mg per kg) and the concentration of use does not cause irritation of the skin or the eyes. It is known to be non-allergenic to the skin and is free from systemic toxicity through the epidermis.
Le choix des oligomères de chlorhydrate d'hexaméthylène biguanide semble être meilleur que celui des sels de chlorhexidine du fait de la très grande instabilité de ces derniers produits à la lumière; en présence de la plupart des tensioactifs ils ont une légère variation du pH, en présence d'hypochlorite ils sont transformés en un colorant indélébile rouge et finalement il y a possibilité de formation de chloraniline, produit considéré comme métabolisant et toxique. L'oligomère de chlorhydrate d'hexa- méthylène biguanide n'a aucun de ces inconvénients. Son pouvoir bactéricide est très élevé et rapide. Une solution de ce produit à 20% dilué à 0,25% (soit 0,05%) détruit en 3 min, à 22°C, 99,99% d'une population microbienne, c'est-à-dire que sur un inoculum initial de 109 microorganismes par ml, il n'est reste que 0,01% soit tout de même 105 microorganismes par ml. Les essais ont été faits entre autres sur Staphylococcus Aureus, Escherichia Coli, Pseudomonas Aerugonosa, Saccharomyces. L'activité germicide est à peine diminuée par la présence de 1 ou 5% de sang, 1 % de lait, 1 % de peptone. Par contre, tout en étant très actif vis-à-vis des bactéries gram+ et gram-, l'oligomère de chlorhydrate d'hexaméthylène biguanide (OCHB) n'est que très peu efficace sur les levures, les moisissures et les champignons. Pour obvier à cette lacune, il a été ajouté à la solution de OCHB une faible quantité d'un ou plusieurs composés d'ammonium quaternaire.The choice of oligomers of hexamethylene biguanide hydrochloride seems to be better than that of chlorhexidine salts because of the very great instability of these latter products in the light; in the presence of most surfactants they have a slight variation in pH, in the presence of hypochlorite they are transformed into an indelible red dye and finally there is the possibility of the formation of chloraniline, a product considered to be metabolizing and toxic. The hexamethylene biguanide hydrochloride oligomer has none of these drawbacks. Its bactericidal power is very high and rapid. A 20% solution of this product diluted to 0.25% (i.e. 0.05%) destroyed in 3 min, at 22 ° C, 99.99% of a microbial population, that is to say that on an initial inoculum of 10 9 microorganisms per ml, only 0.01% remains, which is all the same 10 5 microorganisms per ml. The tests were carried out inter alia on Staphylococcus Aureus, Escherichia Coli, Pseudomonas Aerugonosa, Saccharomyces. The germicidal activity is hardly diminished by the presence of 1 or 5% of blood, 1% of milk, 1% of peptone. On the other hand, while being very active with respect to the gram + and gram- bacteria, the oligomer of hexamethylene biguanide hydrochloride (OCHB) is only very ineffective on yeasts, molds and fungi. To overcome this deficiency, a small amount of one or more quaternary ammonium compounds was added to the OCHB solution.
On a découvert de manière surprenante que les compositions contenant 0,1 à 4% en poids d'un oligomère de chlorhydrate d'hexaméthylène biguanide (OCHB) et de 0,01 à 1,5% en poids de chlorure de didécyldiméthylammonium (CDDA) présentent des activités bactéricides et fongicides très supérieures à celles obtenues en utilisant des quantités équivalentes des produits formant ladite composition. La synergie observée est importante et lesdites compositions ont une action rapide et portée sur la plupart des germes.It has been surprisingly found that compositions containing 0.1 to 4% by weight of an oligomer of hexamethylene biguanide hydrochloride (OCHB) and 0.01 to 1.5% by weight of didecyldimethylammonium chloride (CDDA) exhibit bactericidal and fungicidal activities much higher than those obtained by using equivalent amounts of the products forming said composition. The synergy observed is important and the said compositions have a rapid action which is carried on most germs.
Après addition d'un mélange d'oligomère d'hexaméthylène biguanide (0,15%) et de chlorure de didécyl diméthyl ammonium (0,03%), la baisse de la population microbienne est de 106 après 1 min. de contact (99,9999%). La même solution appliquée sur la main pendant 1 min. laisse 0 survivants sur la surface de la peau (population normale 106). Ce résultat ne peut être obtenu avec aucun produit connu à ce jour, compte tenu des normes imposées, c'est-à-dire absence de toxicité, d'irritation, etc....After addition of a mixture of oligomer of hexamethylene biguanide (0.15%) and didecyl dimethyl ammonium chloride (0.03%), the decrease in the microbial population is 10 6 after 1 min. contact (99.9999%). The same solution applied to the hand for 1 min. leaves 0 survivors on the surface of the skin (normal population 10 6 ). This result cannot be obtained with any product known to date, taking into account the standards imposed, that is to say absence of toxicity, irritation, etc.
Ce mélange convient particulièrement bien quand il est utilisé avec un polymère filmogène, car le film déposé détruit rapidement tous les microorganismes à la surface et reste germicide pendant très longtemps.This mixture is particularly suitable when used with a film-forming polymer, since the deposited film rapidly destroys all microorganisms on the surface and remains germicidal for a very long time.
L'utilisation du didécyl diméthylammonium dans les compositions selon l'invention présente notamment un avantage certain, du fait de son très grand pouvoir mouillant en abaissant la tension superficielle du mélange à 2,81 N/m2 environ.The use of didecyl dimethylammonium in the compositions according to the invention has in particular a certain advantage, because of its very high wetting power by lowering the surface tension of the mixture to 2.81 N / m 2 approximately.
La composition selon l'invention contient de 0,01% à 1,5% de CDDA et de 0,1 à 4% de OCHB. C'est une solution aqueuse et/ou alcoolique.The composition according to the invention contains from 0.01% to 1.5% of CDDA and from 0.1 to 4% of OCHB. It is an aqueous and / or alcoholic solution.
La présente description, en regard des exemples annexés, permettra de mieux comprendre comment l'invention peut être mise en pratique.This description, with reference to the appended examples, will allow a better understanding of how the invention can be put into practice.
Mesure de l'activité bactéricide de l'oligomère de chlorhydrate d'hexaméthylène biguanide (OCHB, n=4 à 7).Measurement of the bactericidal activity of the oligomer of hexamethylene biguanide hydrochloride (OCHB, n = 4 to 7).
On utilise l'OCHB en solution dans de l'eau distillée. On ajoute un inoculum d'un microorganisme à une concentration donnée. Au bout de 3 minutes, on compte les bactéries survivantes et on exprime le résultat en puissance de 10.OCHB is used in solution in distilled water. An inoculum of a microorganism is added at a given concentration. After 3 minutes, the surviving bacteria are counted and the result is expressed as a power of 10.
On obtient le tableau I suivant:
La baisse de microorganismes est donc de 104/ml.The drop in microorganisms is therefore 10 4 / ml.
Mesure de l'activité fongicide du OCHB.Measuring the fungicidal activity of OCHB.
Ce produit est peu actif contre les moisissures et il est nécessaire d'en utiliser de grandes quantités. On inocule de l'extrait d'agar, on laisse à incubation pendant 4 ou 5 jours et on ajoute la concentration de OCHB qui empêche la croissance des germes. On obtient les résultats suivants. (Tableau II)This product is not very active against molds and it is necessary to use large quantities. Agar extract is inoculated, allowed to incubate for 4 or 5 days and the concentration of OCHB which prevents the growth of germs is added. The following results are obtained. (Table II)
Mesure de l'activité bactéricide d'un ammonium quaternaire, à savoir le chlorure de didécyl diméthyl ammonium (CDDA).Measurement of the bactericidal activity of a quaternary ammonium, namely didecyl dimethyl ammonium chloride (CDDA).
On procède comme pour l'exemple 1 a et on obtient les résultats suivants (tableau III) au bout de 1 minute.
Par conséquent on voit que la baisse en microorganismes est de 103 seulement, au bout de une minute.Consequently, it can be seen that the drop in microorganisms is only 10 3 , after one minute.
Mesure de l'activité bactéricide et fongicide d'une composition selon l'invention.Measurement of the bactericidal and fungicidal activity of a composition according to the invention.
On prépare la solution suivante:
On détermine l'activité bactéricide in vivo d'une telle composition.The bactericidal activity in vivo of such a composition is determined.
On obtient le tableau IV qui rassemble les résultats suivants, après application de la solution pendant 1 min.
Ainsi on a une diminution de 106 microorganismes en une minute.Thus there is a decrease of 10 6 microorganisms in one minute.
On voit donc d'une part que l'action de chlorure de didécyl diméthyl ammonium et d'autre part que l'action de l'oligomère sont renforcées. L'activité de la solution selon l'invention est beaucoup plus rapide et importante.It can therefore be seen, on the one hand, that the action of didecyl dimethyl ammonium chloride and, on the other hand, that the action of the oligomer are reinforced. The activity of the solution according to the invention is much faster and greater.
On prépare la solution suivante:
On utilise cette solution comme désinfectant pour le personnel des hôpitaux, les mains des chirurgiens, les surfaces diverses pouvant être contaminées, les appareil de rayons X, les instruments de chirurgie, etc....This solution is used as a disinfectant for hospital staff, the hands of surgeons, various surfaces that may be contaminated, X-ray machines, surgical instruments, etc.
On prépare le mélange suivant:
Cette composition, utilisée à 4% est un des plus puisants stérilisants pour les instruments de chirurgie.This composition, used at 4% is one of the most powerful sterilants for surgical instruments.
Le mélange suivant est préparé:
On prépare une solution de lavage de plaies ou de la peau, ayant la composition ci-dessous:
On mesure l'activité bactéricide de cette composition. On obtient les résultats suivants (tableau V):
On prépare une laque à rémanence d'action ayant la composition suivante:
On détermine l'activité bactéricide selon la méthode de Gashen. Un groupe de trois femmes et de trois hommes se lavent les mains avec du savon pendant une minute, puis ils se rincent celles-ci à l'eau et se les sèchent. Enfin, après 60 min. d'attente, on dénombre la flore sur chaque main. On applique la solution selon l'invention pendant une min. sur chaque main droite, la main gauche servant de référence. On obtient les résultats suivants (tableau VI):
En outre l'activité du désinfectant reste apparemment aussi bonne après port du gant pendant une heure, puisque la population bactérienne reste au même niveau qu'après action du produit pendant une minute. La rémanence d'action est donc très bonne pour cette laque.In addition, the activity of the disinfectant apparently remains as good after wearing the glove for one hour, since the bacterial population remains at the same level as after the action of the product for one minute. The persistence of action is therefore very good for this lacquer.
La solution de laque suivante est préparée:
Ce produit est utilisé pour arroser les surfaces contaminées (tel quel on dilué) et il détruit tous les microorganismes à la surface (bactéries gram+ et -, levures, spores, virus) et forme un léger film ayant une rémanence qui permet de détruire toutes les retombées de germes environnants. Il est utilisé tel quel pour la stérilisation à froid du circuit interne d'appareil d'hemodialyse (rein artificiel), pour la stérilisation à froid des instruments et du matériel de chirurgie, de médecine et d'examen interne (endoscope...). Il détruit à froid tous les microorganismes, bactéries ±, virus, spores, champignons. La présence de polymère polyvinyle pirrolidone permet de garder en suspension les souillures et empêche leur redéposition.This product is used to water contaminated surfaces (as it is diluted) and it destroys all microorganisms on the surface (gram + and - bacteria, yeasts, spores, viruses) and forms a light film having an afterglow which makes it possible to destroy all fallout from surrounding germs. It is used as is for cold sterilization of the internal circuit of hemodialysis machine (artificial kidney), for cold sterilization of surgical, medical and internal examination instruments and equipment (endoscope ...) . It destroys cold all microorganisms, bacteria ±, viruses, spores, fungi. The presence of polyvinyl pirrolidone polymer keeps soilings in suspension and prevents their redeposition.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT81400848T ATE10697T1 (en) | 1980-05-29 | 1981-05-27 | SANITIZING COMPOSITION CONTAINING A QUATERNARY AMMONIUM COMPOUND AND AN OLIGOMER OF HEXAMETHYLENE BIGUANIDE HYDROCHLORIDE. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8011892 | 1980-05-29 | ||
| FR8011892A FR2483177A1 (en) | 1980-05-29 | 1980-05-29 | NOVEL DISINFECTANT COMPOSITION COMPRISING A QUATERNARY AMMONIUM AND A HEXAMETHYLENE BIGUANIDE HYDROCHLORIDE OLIGOMER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0041448A1 EP0041448A1 (en) | 1981-12-09 |
| EP0041448B1 true EP0041448B1 (en) | 1984-12-12 |
Family
ID=9242449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP81400848A Expired EP0041448B1 (en) | 1980-05-29 | 1981-05-27 | Disinfecting composition containing a quaternary ammonium and an oligomer of hexamethylene-diguanide hydrochloride |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0041448B1 (en) |
| JP (1) | JPS5746906A (en) |
| AT (1) | ATE10697T1 (en) |
| AU (1) | AU7098381A (en) |
| CA (1) | CA1164338A (en) |
| DE (1) | DE3167689D1 (en) |
| FR (1) | FR2483177A1 (en) |
| ZA (1) | ZA813565B (en) |
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|---|---|---|---|---|
| US7759327B2 (en) | 2006-01-06 | 2010-07-20 | The Trustees Of Columbia University In The City Of New York | Compositions containing zinc salts for coating medical articles |
| US7871649B2 (en) | 2003-07-17 | 2011-01-18 | The Trustees Of Columbia University In The City Of New York | Antimicrobial compositions containing synergistic combinations of quaternary ammonium compounds and essential oils and/or constituents thereof |
| US7951840B2 (en) | 2002-02-07 | 2011-05-31 | Modak Shanta M | Zinc salt compositions for the prevention of dermal and mucosal irritation |
| US8293802B2 (en) | 2001-10-23 | 2012-10-23 | The Trustees Of Columbia University | Gentle-acting skin-disinfectants and hydroalcoholic gel formulations |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2122900A (en) * | 1982-07-01 | 1984-01-25 | Surgikos Inc | Disinfectant compositions having residual biocidal activity and wipes and sprays containing them |
| FR2552305B1 (en) * | 1983-09-22 | 1985-12-20 | Salkin Andre | HIGH BACTERICIDAL COMPOSITION CONTAINING BIGUANIDE AND PYRIMIDINE |
| CA1259542A (en) * | 1984-09-28 | 1989-09-19 | Francis X. Smith | Disinfecting and preserving solutions for contact lenses and methods of use |
| DE3445901A1 (en) * | 1984-12-15 | 1986-06-19 | Henkel KGaA, 4000 Düsseldorf | LIQUID DISINFECTANT PREPARATIONS WITH BROADBAND EFFECT |
| JPS61146882A (en) * | 1984-12-17 | 1986-07-04 | Dynic Corp | Decorative sheet |
| DE3542516A1 (en) * | 1985-12-02 | 1987-06-04 | Henkel Kgaa | DISINFECTANT |
| GB8625103D0 (en) * | 1986-10-20 | 1986-11-26 | Unilever Plc | Disinfectant compositions |
| EP0324211A1 (en) * | 1988-01-12 | 1989-07-19 | Bosshardt-Chemie AG | Use of compositions for odour removal |
| FR2662174B1 (en) * | 1990-05-15 | 1993-10-15 | Eparco | CLEANING AND DISINFECTION COMPOSITIONS FOR HOUSEHOLD USE WITH HYPOALLERGENIC PROPERTIES AND ARACID CAPACITIES. |
| US5508250A (en) * | 1993-12-07 | 1996-04-16 | Bio-Lab, Inc. | Synergistic antimicrobial compositions containing poly(hexamethylammonium) chloride. |
| FR2718352B1 (en) * | 1994-04-08 | 1996-06-14 | Nicolas Salkind | Bactericidal composition packaged in a water-soluble packaging. |
| FR2759380B1 (en) * | 1997-02-13 | 2002-08-02 | Anios Lab Sarl | DETERGENT AND / OR DISINFECTANT COMPOSITION |
| GB2324467A (en) * | 1997-04-22 | 1998-10-28 | Rhone Poulenc Chemicals | Rapid and long-lasting biocidal system |
| US6303557B1 (en) * | 1999-11-16 | 2001-10-16 | S. C. Johnson Commercial Markets, Inc. | Fast acting disinfectant and cleaner containing a polymeric biguanide |
| JP2001354505A (en) * | 2000-04-13 | 2001-12-25 | Nissan Chem Ind Ltd | Antiseptic mildew-proofing and algae-proofing agent |
| JP2001354504A (en) * | 2000-04-13 | 2001-12-25 | Nissan Chem Ind Ltd | Antiseptic, mildew-proofing and algae-proofing agent |
| US7879365B2 (en) | 2002-02-07 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Zinc salt compositions for the prevention of dermal and mucosal irritation |
| JP2006188451A (en) * | 2005-01-05 | 2006-07-20 | Shoei Kagaku Kk | Antiseptic/fungicidal aqueous preparation of one-pack type |
| EP2359690A1 (en) | 2010-02-23 | 2011-08-24 | East Coast Pharmaceutical Research LLC | Multiplication of the effectiveness of anti-infective agents by a composition including both a dispersant agent and a metal reversal agent |
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Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2611957C2 (en) * | 1976-03-20 | 1985-06-13 | Henkel KGaA, 4000 Düsseldorf | Antimicrobial agents |
| SE425043B (en) * | 1977-05-10 | 1982-08-30 | Kenogard Ab | FUNGICID COMPOSITION, PREFERRED FOR USE AS A THREE PROTECTIVE, CONTAINING AT LEAST ONE QUARTER OF AMMONIUM SUBSTANCE IN MIXING WITH AN AMINE COMPONENT |
| IE47368B1 (en) * | 1977-09-27 | 1984-03-07 | Exterma Germ Prod | Impreganted substrate |
-
1980
- 1980-05-29 FR FR8011892A patent/FR2483177A1/en not_active Withdrawn
-
1981
- 1981-05-25 AU AU70983/81A patent/AU7098381A/en not_active Abandoned
- 1981-05-27 ZA ZA00813565A patent/ZA813565B/en unknown
- 1981-05-27 EP EP81400848A patent/EP0041448B1/en not_active Expired
- 1981-05-27 DE DE8181400848T patent/DE3167689D1/en not_active Expired
- 1981-05-27 AT AT81400848T patent/ATE10697T1/en active
- 1981-05-28 CA CA000378586A patent/CA1164338A/en not_active Expired
- 1981-05-29 JP JP56081189A patent/JPS5746906A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8293802B2 (en) | 2001-10-23 | 2012-10-23 | The Trustees Of Columbia University | Gentle-acting skin-disinfectants and hydroalcoholic gel formulations |
| US8436050B2 (en) | 2001-10-23 | 2013-05-07 | The Trustees Of Columbia University In The City Of New York | Gentle-acting skin-disinfectants and hydroalcoholic gel formulations |
| US7951840B2 (en) | 2002-02-07 | 2011-05-31 | Modak Shanta M | Zinc salt compositions for the prevention of dermal and mucosal irritation |
| USRE45435E1 (en) | 2002-02-07 | 2015-03-24 | The Trustees Of Columbia University In The City Of New York | Zinc salt compositions for the prevention of dermal and mucosal irritation |
| US7871649B2 (en) | 2003-07-17 | 2011-01-18 | The Trustees Of Columbia University In The City Of New York | Antimicrobial compositions containing synergistic combinations of quaternary ammonium compounds and essential oils and/or constituents thereof |
| US9421263B2 (en) | 2003-07-17 | 2016-08-23 | The Trustees Of Columbia University In The City Of New York | Antimicrobial compositions containing synergistic combinations of quaternary ammonium compounds and essential oils and/or constituents thereof |
| US7759327B2 (en) | 2006-01-06 | 2010-07-20 | The Trustees Of Columbia University In The City Of New York | Compositions containing zinc salts for coating medical articles |
| US8207148B2 (en) | 2006-01-06 | 2012-06-26 | The Trustees Of Columbia University In The City Of New York | Compositions containing zinc salts for coating medical articles |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7098381A (en) | 1981-12-03 |
| ATE10697T1 (en) | 1984-12-15 |
| FR2483177A1 (en) | 1981-12-04 |
| CA1164338A (en) | 1984-03-27 |
| JPS5746906A (en) | 1982-03-17 |
| EP0041448A1 (en) | 1981-12-09 |
| DE3167689D1 (en) | 1985-01-24 |
| ZA813565B (en) | 1982-06-30 |
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